This invention relates to novel derivatives of N-trichloroacetyl-N'-chlorobenzoylhydrazine, having the following formula (I). ##STR2##
where n stands for 1 or 2, and especially adapted for use as fungicidal agent for agricultural use, and process for manufacturing same.
As N-substituted-N'-chlorobenzoylhydrazine derivatives, hitherto are known N-acetyl-N'-chlorobenzoylhydrazine derivatives, but those of trichloroacetyl-substituted type or more specifically those of the form of N-trichloroacetyl-N'-chlorobenzoylhydrazine are not yet known according to our knowledge.
We have newly synthesized these unknown N-trichloroacetyl-N'-chlorobenzoylhydrazine derivatives, investigated thereinto and found that these novel compounds have highly superior fungicidal effect with respect to various agricultural plant diseases.
It is, therefore, an object of the present invention to provide novel N-trichloroacetyl-N'-benzoylhydrazine derivatives.
A further object is to provide a composition including at least one of the above-mentioned novel compounds as the fungicidally effective substance adapted for the control of agricultural plant diseases.
Still a further object is to provide a process for the preparation of the above group of novel compounds.
The novel derivatives of the above kind may be grouped as shown in the following Table I.
Table I __________________________________________________________________________ Compound No. Structural Formula Naming M.P. Yield* __________________________________________________________________________ ##STR3## N-trichloroacetyl-N'-2- chlorobenzoylhydrazine 168 - 170.degree. C 57% 2 ##STR4## N-trichloroacetyl-N'-3- chlorobenzoylhydrazine 143 - 144.degree. C 76% 3 ##STR5## N-trichloroacetyl-N'-4- chlorobenzoylhydrazine 165 - 166.degree. C 70% 4 ##STR6## N-trichloroacetyl-N'-2,4- dichlorobenzoylhydrazi ne 149 - 150.degree. C 80% 5 ##STR7## N-trichloroacetyl-N'-2,5- dichlorobenzoylhydrazi ne 127 - 130.degree. C 51% 6 ##STR8## N-trichloroacetyl-N'-3,4- dichlorobenzoylhydrazi ne 183 - 185.degree. C 50% __________________________________________________________________________
For the preparation of the said novel derivatives, the following steps may be employed: ##STR9##
(where n stands for an integer of 1 or 2)
More specifically, chloro-substituted benzoic ester of the above formula (1) and hydrazine hydrate are agitated and heated in a solvent such as alcohol to provide a corresponding acid hydrazide which is then added in a benzene phase, droppingly with equimolar amount of trichloroacetylchloride in the presence of equimolar amount of triethylamine and then the reaction mixture is agitated at room temperature for 1-7 hours to provide the desired final product.
In the following, the above preparing process will be described more in detail with reference to several preferred numerical examples.